A Single Nickel Catalyst for the Acceptorless Dehydrogenation of Alcohols and Hydrogenation of Carbonyl Compounds

被引：112

作者：

Chakraborty, Sumit ^{[1
]}

Piszel, Paige E. ^{[1
]}

Brennessel, William W. ^{[1
]}

Jones, William D. ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

ORGANOMETALLICS | 2015年 / 34卷 / 21期

基金：

美国国家科学基金会;

关键词：

IRIDIUM COMPLEXES; OXIDATION; RUTHENIUM; HETEROCYCLES; LIGANDS; IMINES; BEARING; SYSTEM; OSMIUM; WATER;

D O I：

10.1021/acs.organomet.5b00824

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A single homogeneous nickel(II) complex, supported by the tris(3,5-dimethylpyrazoly)borate ligand and 2-hydroxyquinoline ancillary ligand, is shown to catalyze both acceptorless dehydrogenation of alcohols and hydrogenation of carbonyl compounds under mild conditions. Products from the catalytic reactions were isolated with good yields. A mechanistic investigation highlights the critical role of the 2-hydroxyquinoline ligand in the catalysis and argues against a stepwise dehydrogenation pathway.

引用

页码：5203 / 5206

页数：4

共 41 条

[1] Ruthenium-catalyzed Oppenauer-type oxidation of 3 beta-hydroxy steroids. A highly efficient entry into the steroidal hormones with 4-en-3-one functionality [J].

Almeida, MLS ;

Kocovsky, P ;

Backvall, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) :6587-6590

[2] Osmium and Ruthenium Catalysts for Dehydrogenation of Alcohols [J].

Bertoli, Marcello ;

Choualeb, Aldjia ;

Lough, Alan J. ;

Moore, Brandon ;

Spasyuk, Denis ;

Gusev, Dmitry G. .

ORGANOMETALLICS, 2011, 30 (13) :3479-3482

[3] (CYCLOPENTADIENONE)RUTHENIUM CARBONYL-COMPLEXES - A NEW CLASS OF HOMOGENEOUS HYDROGENATION CATALYSTS [J].

BLUM, Y ;

CZARKIE, D ;

RAHAMIM, Y ;

SHVO, Y .

ORGANOMETALLICS, 1985, 4 (08) :1459-1461

[4] Reversible catalytic dehydrogenation of alcohols for energy storage [J].

Bonitatibus, Peter J., Jr. ;

Chakraborty, Sumit ;

Doherty, Mark D. ;

Siclovan, Oltea ;

Jones, William D. ;

Soloveichik, Grigorii L. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2015, 112 (06) :1687-1692

[5] Well-Defined Iron Catalysts for the Acceptor less Reversible Dehydrogenation-Hydrogenation of Alcohols and Ketones [J].

Chakraborty, Sumit ;

Lagaditis, Paraskevi O. ;

Foerster, Moritz ;

Bielinski, Elizabeth A. ;

Hazari, Nilay ;

Holthausen, Max C. ;

Jones, William D. ;

Schneider, Sven .

ACS CATALYSIS, 2014, 4 (11) :3994-4003

[6] A Molecular Iron Catalyst for the Acceptorless Dehydrogenation and Hydrogenation of N-Heterocycles [J].

Chakraborty, Sumit ;

Brennessel, William W. ;

Jones, William D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (24) :8564-8567

[7] Resolving Heterogeneity Problems and Impurity Artifacts in Operationally Homogeneous Transition Metal Catalysts [J].

Crabtree, Robert H. .

CHEMICAL REVIEWS, 2012, 112 (03) :1536-1554

[8] Dehydrogenation as a Substrate-Activating Strategy in Homogeneous Transition-Metal Catalysis [J].

Dobereiner, Graham E. ;

Crabtree, Robert H. .

CHEMICAL REVIEWS, 2010, 110 (02) :681-703

[9] Hydrogen bonding and anion binding in structures of tris(pyrazolyl)boratenickel(II) and phosphate esters [J].

Dolores Santana, M. ;

Lopez-Banet, Luisa ;

Garcia, Gabriel ;

Garcia, Luis ;

Perez, Jose ;

Liu, Malva .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2008, (25) :4012-4018

[10] Direct Access to POP-Type Osmium(II) and Osmium(IV) Complexes: Osmium a Promising Alternative to Ruthenium for the Synthesis of Imines from Alcohols and Amines [J].

Esteruelas, Miguel A. ;

Honczek, Nicole ;

Olivan, Montserrat ;

Onate, Enrique ;

Valencia, Marta .

ORGANOMETALLICS, 2011, 30 (09) :2468-2471

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